JP5637707B2 - スキルプシンb含有組成物及びスキルプシンb含有組成物の製造方法 - Google Patents
スキルプシンb含有組成物及びスキルプシンb含有組成物の製造方法 Download PDFInfo
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- 244000288157 Passiflora edulis Species 0.000 claims description 53
- 235000000370 Passiflora edulis Nutrition 0.000 claims description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
- 239000002904 solvent Substances 0.000 claims description 45
- 238000000605 extraction Methods 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
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- 238000000034 method Methods 0.000 description 9
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- 230000014759 maintenance of location Effects 0.000 description 5
- 241000218996 Passiflora Species 0.000 description 4
- IIXHQGSINFQLRR-UHFFFAOYSA-N Piceatannol Natural products Oc1ccc(C=Cc2c(O)c(O)c3CCCCc3c2O)cc1O IIXHQGSINFQLRR-UHFFFAOYSA-N 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
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- 230000002401 inhibitory effect Effects 0.000 description 4
- CDRPUGZCRXZLFL-OWOJBTEDSA-N piceatannol Chemical group OC1=CC(O)=CC(\C=C\C=2C=C(O)C(O)=CC=2)=C1 CDRPUGZCRXZLFL-OWOJBTEDSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000309464 bull Species 0.000 description 3
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- 235000015110 jellies Nutrition 0.000 description 3
- 239000008274 jelly Substances 0.000 description 3
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- MTYSFTYBAMMIGE-HNQUOIGGSA-N 4-[(e)-2-[2-(3,4-dihydroxyphenyl)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2,3-dihydro-1-benzofuran-4-yl]ethenyl]benzene-1,2-diol Chemical compound C=1C(O)=CC=2OC(C=3C=C(O)C(O)=CC=3)C(C=3C=C(O)C=C(O)C=3)C=2C=1\C=C\C1=CC=C(O)C(O)=C1 MTYSFTYBAMMIGE-HNQUOIGGSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- MTYSFTYBAMMIGE-IZLXSDGUSA-N Scirpusin B Natural products Oc1cc(O)cc(c1)[C@H]2[C@@H](Oc3cc(O)cc(C=Cc4ccc(O)c(O)c4)c23)c5ccc(O)c(O)c5 MTYSFTYBAMMIGE-IZLXSDGUSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 102000004139 alpha-Amylases Human genes 0.000 description 2
- 108090000637 alpha-Amylases Proteins 0.000 description 2
- 229940024171 alpha-amylase Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000036436 anti-hiv Effects 0.000 description 2
- 235000012970 cakes Nutrition 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
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- 238000010828 elution Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- -1 polyphenol compound Chemical class 0.000 description 2
- MTYSFTYBAMMIGE-UHFFFAOYSA-N scirpusin B-cis Natural products C=1C(O)=CC=2OC(C=3C=C(O)C(O)=CC=3)C(C=3C=C(O)C=C(O)C=3)C=2C=1C=CC1=CC=C(O)C(O)=C1 MTYSFTYBAMMIGE-UHFFFAOYSA-N 0.000 description 2
- 238000000825 ultraviolet detection Methods 0.000 description 2
- 241001264746 Callistemon rigidus Species 0.000 description 1
- 241000834295 Caragana rosea Species 0.000 description 1
- 241000834297 Caragana tibetica Species 0.000 description 1
- 240000006766 Cornus mas Species 0.000 description 1
- 235000003363 Cornus mas Nutrition 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 244000103034 Scirpus californicus Species 0.000 description 1
- 235000014326 Scirpus californicus Nutrition 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 108010093894 Xanthine oxidase Proteins 0.000 description 1
- 102100033220 Xanthine oxidase Human genes 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
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- 235000015895 biscuits Nutrition 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 230000037319 collagen production Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000011850 desserts Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
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- 238000002523 gelfiltration Methods 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- 230000008099 melanin synthesis Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
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- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000015927 pasta Nutrition 0.000 description 1
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- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
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- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- 239000003064 xanthine oxidase inhibitor Substances 0.000 description 1
Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Furan Compounds (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Description
・ カラム:ODS-3 径4.6mm、長さ150mm(ジーエルサイエンス株式会社製)
・ カラム温度:45℃
・ 溶出条件:流速0.75ml/min、15%アセトニトリル(0min)→40%アセトニトリル(20min)→45%アセトニトリル(25min)
・ UV検出:280nm
パッションフルーツ種子を凍結乾燥粉砕させた粉砕物(30〜60メッシュパス)の60gに80%アセトンの200mlを添加し、室温で攪拌して種子抽出液を作製した。これを、ODSカラムを用いたHPLCによって分画した。HPLCによる分画条件は、以下のとおりとした。
・ カラム:ODS-3 径20mm、長さ250mm(ジーエルサイエンス株式会社製)
・ カラム温度:室温
・ 溶出条件:流速5ml/min、10%アセトニトリル(0min)→50%アセトニトリル(70min)→80%アセトニトリル(75min)→80%アセトニトリル(90min)
・ UV検出:280nm
1H NMR(CD30D, 500MHz):δ4.38 (1H,d, J=6.0Hz), δ5.32((1H,d, J=6.0Hz), δ6.19(2H,d, J=2.2Hz), δ6.21(1H,t, J=2.0Hz), δ6.30(1H,d, J=6.0Hz), 6.58(1H,d, J=16.1Hz), 6.62(1H,dd, J=2.2, 8.5Hz) 6.66(1H,d, J=1.9Hz), δ6.68(1H,d, J=7.8Hz), 6.74(1H,d, J=2.2Hz) 6.78(1H,d, J=8.2Hz), 6.81 (1H,d, J=16.4Hz), δ6.80(1H,d, J=1.9Hz) ;
13C NMR: (CD3OD, 125MHz):δ:58.1, 94.8, 96.8, 102.2, 104.4, 107.3x2, 113.6, 114.0, 116.2x2, 116.3, 118.4, 119.8, 120.0, 123.6,δ: 130.9, 131.0, 134.9, 137.0, 146.3, 146.4, 146.5, 146.6, 147.6, 159.8x3, 162.7
パッションフルーツ種子からのスキルプシンBの抽出方法について検討した。具体的には、下記の抽出方法で、スキルプシンBの抽出効率を調べた。
粉砕した種子の60gに80%含水エタノール200mlを加え、30分間室温にて振とうし、抽出を行い、その上清を回収した。この工程を2回繰り返した。更に、その残渣固形物に80%含水アセトンの200mlを加え、30分間室温にて振とうし、抽出を行い、その上清を回収した。この工程を3回繰り返した。そして回収した上清を集めて得られた抽出液を濃縮し、80%含水エタノールで200mlに定容し、その10μlを分析用HPLCにかけた。そして、あらかじめ高純度に精製したもの(97%)を標準として検量線を作成し、その抽出物に含まれるスキルプシンBの量を定量した。
粉砕した種子の300gに80%、90%、又は95%の含水エタノール3Lを加え、92℃で90分間加熱還流抽出を行った。そして、得られた抽出液を濃縮し、80%含水エタノールで200mlに定容し、その10μlを分析用HPLCにかけた。そして、あらかじめ作成した検量線により、その抽出物に含まれるスキルプシンBの量を定量した。
Claims (5)
- パッションフルーツ種子から、アルコールを20〜99.9体積%含む含水アルコール系溶媒及びケトンを20〜99.9体積%含む含水ケトン系溶媒から選ばれた少なくとも1種を抽出溶媒として用いて振とうあるいは加熱還流抽出した後にスキルプシンBを分画及び/又は精製することにより得られ、スキルプシンBを固形分中40〜99.9質量%の含有量で含むことを特徴とするスキルプシンB含有組成物。
- パッションフルーツ種子を粉砕した後、アルコールを20〜99.9体積%含む含水アルコール系溶媒及びケトンを20〜99.9体積%含む含水ケトン系溶媒から選ばれた少なくとも1種を添加して、振とうあるいは加熱還流し、前記溶媒中にスキルプシンBを抽出することを特徴とするスキルプシンB含有組成物の製造方法。
- 前記パッションフルーツ種子は、パッションフルーツの生の種子又はパッションフルーツの生の種子を乾燥した種子である請求項2記載のスキルプシンB含有組成物の製造方法。
- 前記含水アルコール系溶媒が含水エタノールであり、又は前記含水ケトン系溶媒が含水アセトンである請求項2又は3記載のスキルプシンB含有組成物の製造方法。
- 抽出後、溶媒を減圧留去する請求項2〜4のいずれか1つに記載のスキルプシンB含有組成物の製造方法。
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JP2010063027A JP5637707B2 (ja) | 2010-03-18 | 2010-03-18 | スキルプシンb含有組成物及びスキルプシンb含有組成物の製造方法 |
US14/111,476 US9376416B2 (en) | 2010-03-18 | 2011-04-22 | Composition containing scirpusin B, and process for producing composition containing scirpusin B |
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JP5637707B2 true JP5637707B2 (ja) | 2014-12-10 |
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JP5830529B2 (ja) * | 2011-04-22 | 2015-12-09 | 森永製菓株式会社 | スキルプシンb含有組成物及びスキルプシンb含有組成物の製造方法 |
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JP6294579B2 (ja) * | 2012-01-25 | 2018-03-14 | 森永製菓株式会社 | グルタチオン産生促進剤 |
JP6343126B2 (ja) * | 2013-05-14 | 2018-06-13 | 森永製菓株式会社 | 植物抽出物またはその溶液に含まれるスチルベン類の安定化方法、及び、スチルベン類を含有した植物抽出物またはその溶液 |
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JPH1180148A (ja) * | 1997-09-02 | 1999-03-26 | Kikkoman Corp | プロアントシアニジンの製造法 |
JP5415037B2 (ja) * | 2007-10-04 | 2014-02-12 | 森永製菓株式会社 | コラーゲン産生促進剤 |
JP5430891B2 (ja) * | 2007-10-04 | 2014-03-05 | 森永製菓株式会社 | メラニン生成抑制剤 |
JP2010030911A (ja) * | 2008-07-25 | 2010-02-12 | Morinaga & Co Ltd | コラーゲン産生促進剤 |
BRPI0925037B1 (pt) * | 2009-04-03 | 2018-06-12 | Morinaga & Co., Ltd. | Método de produzir uma composição contendo piceatanol |
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